Step by Step Guide to Planning Your First Solo Trip

After you’ve read my post on the most common questions about solo travel and you’re ready to go off on your own adventure, how do you actually get started? In this post, I’ll take you through my workflow/thought process from start to finish. Everything from how I choose a destination to how and what I pack.  

Choosing your destination

This might be the toughest part.  You’re staring at a map of the world and you’re so excited to go SOMEWHERE that you’re blindly throwing darts at the map.  When you hit a country, you find every reason why you CAN’T go to that country that you only succeed in wasting time.

The point of your first trip is to get comfortable and understand the routine to establish the building blocks for future trips.  If you’re completely overwhelmed, you won’t enjoy your trip and you’ll probably be looking for a way to get home as soon as possible. I’ve seen and heard stories of people who were so excited about their first solo trip but had done zero prep for it. When they got there, they couldn’t figure out anything and either thought or were getting scammed everywhere that they just hated it. After a couple days, they were ready to come home vowing never to do it again.

Don’t consume yourself with the destination.  I would start with a basic outline of where you’d like to go and be honest with what your comfort level is.  Assuming you’ve already tested the waters with a short trip somewhere, think about the type of country you want to visit.  Are you comfortable with language barriers or would you like to start with an English speaking country? I wouldn’t recommend going to a remote island in Indonesia on your first trip if you don’t have some knowledge of the language because you’ll probably be completely overwhelmed.  

I have a list of places I’d like to visit.  Any time I see something remotely interesting, I add it to the list.  It can be a country, city, a place, sporting event, food I want to eat, etc.  Basically ANYTHING. My list currently has random things like the Monaco Grand Prix, the Church of Tigray, the Bolivian salt flats to name a few.   It’s just a starting point. From the list, I’ll start keeping an eye open for flight deals, look for award flight availability, and see where in the tourism cycle it is (peak tourist season or off season?).  

The price of the flight and/or the award flight availability is the determining factor of where I’m going.  Usually if flights are available, it’s because tourism is low and that is a major selling point for me. Does this mean I’m sometimes going to destinations that aren’t on my list?  Absolutely. But who cares? It’s new and exciting.

Once you find a fare that meets your level of comfort, book the flight.  This has you committed and now you have skin the game. The first step is the toughest so once you’ve committed, the rest will just be filling in the blanks because you’re working with something concrete.  

Your flights determine the length of time for your trip.  If you’re looking for the cheapest option, just use the calendar function when searching and the lowest prices should pop up.  You’ll more than likely be flying out on a Tuesday, Wednesday, or Thursday and returning on one of those days as well for the cheapest fares.

Side note.  If you happen to stumble across an error fare, I would recommend that you book that IMMEDIATELY.  Find some random dates that might work and then worry about everything else later. You have 24 hours to cancel your flight for a full refund so act now and ask questions later.

Flights are booked.  Now what?

This part is the planning phase and I think of it in 3 parts.

  • determining which sites are interesting
  • actually getting a visa(s) if necessary
  • purchasing tickets to any major events or attractions

Planning what to visit

Next thing I do is check the area(s) you want to visit and determine how to split up your time.  For example, let’s say you found a great deal to Peru. Assuming you want to visit Machu Picchu, and you have 7 days of travel, you’ll need to figure out what you want to do and where you want to go.  Do you want to spend the entire time in Cusco or do you want to go visit other cities? 7 days is plenty of time to visit Machu Picchu and explore Cusco as well as another city like Arequipa. Or do you keep it simple and stay in Lima since you’ll more than likely be flying there first? Is Lima worth the time or would you rather visit another city?

This is where you do all your research and figure out an itinerary that works. A more substantial and detailed plan of action.

Buying tickets for domestic flights is much simpler since those fly more frequently than international flights and if you’re going some place with great rail service, life is even easier since that takes virtually zero planning.

Now if you’re going to a country where you’ll have to fly or ride a bus, you’ll need to make sure you allot the proper amount of time to get to your destination.  Time is limited so you’ll have to figure out what is the best transportation method for your timeframe vs. money. At this stage, you’re just trying to find the destinations you want to visit and NOT BOOKING anything (with one caveat listed below).  You’re just interested in seeing what’s around, how you would potentially get there, and the time it’ll take.

Check for Visas

This obviously depends on which country issued your passport as some countries can visit visa free more easily than others. You’ll also want to see if you’ll need a visa prior to arrival and if so, how long it takes and any requirements needed for your passport.  If you can get one on arrival, thats super easy. Just get one before you walk through immigration. Some common rules are you need at least 6 months validity before your passport expires and at least 2 blank pages for your visa but each country is different.  Depending on how long it takes, you might want to get started on this now.

Another thing to note.  Some countries require you to provide your flight plans and even hotel names of where you’ll stay.  You can typically just get around this by booking a refundable hotel somewhere as a placeholder until you figure out your ultimate plans.  

If the country you’re going to has E Visas or visa on arrival, you’ll be in an easier spot.  But if you booked an open jaw ticket (flying into one city and flying out of another), you may need to have proof that you’re leaving the country on a specific date/flight.  You can do this by just booking a random flight online somewhere and then cancelling it as soon as you get through immigration.

Book Tickets to any MAJOR events or attractions

Here is the caveat. If there are any events or attractions you want to see and worried about tickets, you’ll want to book those ASAP.  The event is basically going to serve as your cornerstone and you’ll basically plan your trip around this single event.  Why? Because the event is probably going to be the highlight and the most expensive activity you do. You’ll want to maximize the experience as well as not miss it.  

Going back to our Peru example, you’ll want to purchase your ticket to Machu Picchu early because there is a daily limit and they sell out quickly.  Then you’ll want to purchase your train ticket because there are only so many ways you can get there and a limited number of seats on a train. Since Machu Picchu is the highlight of the trip, you’ll want to make sure you get to Cusco with enough time to prepare for the trip (if you’re staying there) and allow for any delays because if you miss your allotted time frame, you won’t be able to go.

An example of a major event would be something like Wimbledon in London. Although you can buy a ticket for just a grounds pass, if your lifelong dream is to sit at Centre Court and watch the men’s final, you’ll want to purchase a ticket as soon they become available and plan your trip around that event. You certainly wouldn’t want to spend all that money only to miss it because you were stuck in Paris since you missed your Eurostar train and didn’t plan accordingly.

This all sounds obvious but I’ve run into so many people who thought they had plenty of time to get somewhere only to mismanage their time and completely miss the event they planned their entire trip around.  Don’t make the mistake of trying to do too much when there is something big at stake.

This is the time you’ll want to plan.  Very few items are booked and finalized but you need to make sure you have everything necessary since things like getting a visa is simple but time consuming.  And the last thing you want is to be caught off guard with no ability to enter a country because you didn’t plan ahead.

2-3 weeks before departure

Finalize your destinations and start looking for hostels, hotels, airbnbs, etc in those areas.  As a solo traveler, make sure you’ve done your research on which areas are safe (if you’re walking home alone at night, you don’t want to be in a dodgy part of town).  

Make sure you know how long it’s going to take to get from one city to another.  If you’re going long distance on a train or bus, you may want to take the overnight option and pay a little extra for a sleeper cabin or a first class bus seat (especially if you’re in South America which is totally worth it for the price).  

Depending on how you like to do things, you could just book your room when you get to town especially if you’re going the airbnb or hostel route.  I prefer to have a hotel booked so I don’t have to worry about anything when I arrive but this is totally up to you.

For any short flights, you may want to start looking into this around now and booking them before the price goes up.  Trains and busses don’t matter since you can just get a ticket before departure.

This is also when I start looking at the forecast since it’ll give me a fairly accurate idea of what the weather will be like when I’m there.  

1 day before

Pack.  But here is the packing strategy.  Pack what you know you’ll need for 4 days.  That‘s it. If you still have space in your bag after you get everything in, then you might think about taking it.  Remember you’re traveling solo and you’re responsible for getting your bag on/off planes, trains, and busses let alone walking around.  Don’t make it harder on yourself.

An easy way to approach this is to think what the likelihood is of you using a particular item every day.  If you aren’t going to use it every day, leave it at home. If you need one, just buy it there.  If the forecast is for rain 2 days, buy an umbrella there vs taking one with you.

Obviously don’t take your massive shampoo bottles or big tubes of toothpaste (I’ve seen it!) and consolidate everything you can into as few containers as possible.  I usually like to consolidate all my pills like Advil and chewable tablets for upset stomach, etc. into one bottle (but choose different colored or sized pills to tell them apart).

Check with your hotel to see if they have a shuttle service that can pick you up from the airport. It may come at a cost and it won’t be the cheapest option, but it’ll be the easiest option and one less thing to worry about when you step out of the arrivals terminal. You’ll be inundated with people asking if you need a taxi as they prey on unknowing tourists with fists full of money just ready to be scammed. Once you’re in the city, you can take your time to figure out the public transportation system.

I also try to pick a restaurant or an eatery somewhere close to the hotel. I don’t enjoy eating at hotels so I try pick out a spot somewhere on Google maps that looks walkable from the hotel. Depending on how long your travel day is and your arrival time, there’s a good chance you’ll just want to eat and take it somewhat easy.

Download any maps so you can use them even if offline. You never know when you’ll be in an internet dead zone and you don’t want to be caught without a map. It rarely happens if you’re in a densely populated area but happens quite a bit if you’re in rural parts of a country.

Departure/Travel Day

Take your passport and go!  All the planning is done so the only thing you have to do is get to the airport on time.

Final thoughts

Hopefully this gives you an idea of my workflow/thought process whenever I travel.  No matter how many times I travel, the workflow remains the same. It keeps me on task and gives me a clear idea of what to do.  Of course plans can change and I may decide to stay in a specific area for a longer or shorter period of time.

By first knowing the firm dates of your arrival and departure, you can then fill in the blanks to meet your situation. The amount of time you have is dependent on each individual but for our first solo trip, I think it’s better to have firm parameters so you know there is an end in sight. If you don’t like it, you can count down the days. But if you find yourself really enjoying it, you can start planning for your next trip on the flight home.

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